Devil's Advocate

Get a critique from an outside model (Google Gemini 3.1 Pro by default) to pressure-test work before it ships. The whole reason this skill exists is that Claude and the user may share the same blind spots after working on a piece of content together. Sending the work to a model in a different lineage surfaces weaknesses that neither of you will catch alone.

Never substitute your own critique for this tool. If you find yourself about to write "here's what I think the weak points are" without running the script, stop — you are defeating the entire purpose of the skill.

When to use this skill

Use it when the user explicitly asks for a second opinion, a devil's advocate read, or to poke holes in something. Also proactively suggest it when:

• The team is about to ship high-stakes work (a public launch plan, board-level messaging, a pricing decision, a bet-the-quarter campaign).
• You and the user have been iterating for a while and the work feels "done" — fresh eyes matter most when confirmation bias is strongest.
• the user is weighing a decision with several defensible answers (positioning shift, channel bet, org change).
• A plan makes a claim that would be expensive to get wrong (projected pipeline, headcount, conversion lift).

Do NOT reach for this skill for quick copy edits, tactical wordsmithing, or requests the user clearly wants done inside Claude. This is a heavier tool meant for moments where an outside critique has real value.

Prerequisites

• GOOGLE_AI_STUDIO_API_KEY is already in the repo .env (shared with image-gen and youtube-thumbnail).
• The script uses only the Python standard library. No installs required.

If the key is missing, the script will exit with a clear error and a link to create one.

How to run it

The script lives at .claude/skills/devils-advocate/scripts/challenge.py.

1. Critique files

Most common case. Pass one or more files you want challenged:

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --files marketing/plans/pipeline-growth-strategy.md

Multiple files are fine — the critic reads them together and judges them as one body of work:

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --files marketing/landing-pages/trial/hero.html marketing/landing-pages/trial/proof.html

2. Critique an inline statement, decision, or assumption

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --statement "We should move our LinkedIn cadence from 3x/week to daily because engagement rose 18% in Q1."

3. Critique content piped in

cat draft.md | python3 .claude/skills/devils-advocate/scripts/challenge.py --stdin

4. Give the critic supporting context

This is where the skill gets sharp. The critic produces much better work when it knows the positioning, the ICP, and the brief. For branded work, pass the relevant brain files as context so the critique is judged against our actual strategy and audience:

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --files marketing/plans/newsletter-monthly.md \
  --context-files brain/positioning-and-messaging.md brain/audience-language.md \
  --note "Audience: platform engineers at 500-5000 employee companies. Goal: signups for the newsletter as a pipeline top-of-funnel. Cadence: monthly."

Rules of thumb for --context-files:

• Always consider adding brain/positioning-and-messaging.md for any marketing content — it keeps the critic inside our ICP and message pillars.
• Add brain/truth.md when the work makes product claims, so the critic can flag invented facts.
• Add brain/audience-language.md when voice/tone is part of the critique.
• For campaign plans, also add the matching plan file (e.g. marketing/plans/pipeline-growth-strategy.md) if the target work should tie into it.
• Don't dump everything in brain/ as context. Pick the files that actually apply.

5. Save the critique to a file

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --files marketing/plans/newsletter-monthly.md \
  --context-files brain/positioning-and-messaging.md \
  --out marketing/reviews/newsletter-monthly-devils-advocate.md

Default location for saved critiques: marketing/reviews/<target-name>-devils-advocate.md.

6. Override the model

Default is gemini-3.1-pro-preview. Other text-capable models on our key include gemini-3-pro-preview, gemini-2.5-pro, gemini-pro-latest. Use a different model only if the user asks, or if the default times out / fails.

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --files plan.md --model gemini-2.5-pro

Picking the target type

The script auto-detects a target-type hint from the file extensions and paths, but you can set it explicitly with --target-type:

Set this explicitly when the default guess would be wrong. For example, if you pass a .html file from marketing/templates/ and you want it judged as rendered content (not code), pass --target-type content.

What the output looks like

The critic always returns Markdown with these sections, in order:

1. Steelman — the strongest honest case FOR the work.
2. What the work is actually claiming — a literal restatement, to prevent strawmanning.
3. Specific weaknesses — numbered list with Location, Problem, Why it matters, Fix or test.
4. Counter-evidence and missing evidence — what would weaken the argument, what should be cited.
5. Alternative framings — one or two different angles, with tradeoffs.
6. Risks and failure modes — realistic ways it backfires, ranked.
7. Bottom line — one of SHIP, SHIP WITH FIXES, REWORK, KILL, plus one sentence of reasoning.

The top of the file is a comment tag identifying which model produced the critique and what target type was assumed, so reviews stay traceable.

After you get a critique

Do not silently accept every point the critic makes. It is an outside voice, not an oracle. Your job after running it is:

1. Read the critique end to end. Don't skim.
2. Flag which specific items you agree with, disagree with, and want the user to decide. Being concrete is the whole value — "the Q1 engagement lift isn't enough evidence for a 3x cadence change" is useful; "it raises good points" is useless.
3. Ask the user which ones he wants to act on before editing. Some critiques are from a model that doesn't know the company as deeply as you do; others expose real problems you missed.
4. When the user says go, make the specific changes. Don't rewrite from scratch unless the critique says REWORK and the user agrees.

If the critic returns SHIP, that's a useful signal — but still read the weaknesses section. Good critiques say SHIP with caveats; bad critiques either rubber-stamp or gratuitously complain. Treat suspicious uniformity (all SHIP, all KILL) as a signal to re-run with different context.

Example invocations

A blog draft:

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --files marketing/blog/2026-04-monitoring-is-dead.md \
  --context-files brain/positioning-and-messaging.md brain/audience-language.md \
  --note "Author: CTO voice. Goal: drive inbound demo requests from security engineers."

A positioning statement (inline):

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --statement "[Company] is the only platform that detects AI agent attacks in real time without instrumenting the agent itself." \
  --context-files brain/positioning-and-messaging.md brain/truth.md \
  --target-type positioning

A HubSpot template:

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --files marketing/templates/email-templates/newsletter-monthly-email.html \
  --target-type code \
  --note "Must render in Outlook 2019, dark mode iOS Mail, and Gmail web."

A campaign plan with full context:

python3 .claude/skills/devils-advocate/scripts/challenge.py \
  --files marketing/plans/pipeline-growth-strategy.md \
  --context-files brain/positioning-and-messaging.md brain/customer-journey.md \
  --out marketing/reviews/pipeline-growth-strategy-devils-advocate.md

Failure modes to watch for

• API timeout or 5xx. Retry once. If it keeps failing, try --model gemini-2.5-pro as a fallback.
• Critique that reads like a rewrite request. The critic sometimes slips into copy-editing mode. Re-run with --note "do NOT rewrite prose; challenge logic, evidence, and risk only."
• Critique that doesn't know the company. Add brain/positioning-and-messaging.md and brain/truth.md to --context-files and re-run.
• Critique that contradicts something in our brain files. Trust the brain; flag the disagreement to the user rather than editing to match the critic.